


Regular Check-Ins

by dianapowerslit



Category: Supernatural
Genre: Caring Dean Winchester, Developing Relationship, Explicit Sexual Content, F/M, Fluff and Smut, Masturbation, Oral Sex, Porn With Plot, Reader-Insert, Self-Esteem Issues, Sex, Smut
Language: English
Status: Completed
Published: 2018-07-03
Updated: 2018-07-03
Packaged: 2019-06-01 15:36:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,246
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15146264
Author URL: https://archiveofourown.org/users/dianapowerslit/pseuds/dianapowerslit
Summary: You and Dean have been friends since he saved your life, but is there more there?  Is it mutual?





	Regular Check-Ins

**Author's Note:**

> I do not own Dean Winchester as a character or any other established characters, but the story is original as is the reader insert character. Please be kind and don't steal as it stifles creativity. Also, please leave me comments and let me know what you think. This is my first posting here, so hopefully it goes over well. I am also open to requests for other stories in the future, so feel free to shoot me a message (see end of work for how).

And, there he was again at your door. Dean gazed at you easily and you felt the calm that he always brought with him. It wasn’t the first time he had come to check on you since your whole family was slaughtered, but every time it made you feel better. It probably shouldn’t have because the memories of that horrible night always came back to you, but there was something about the green-eyed hunter that made you feel better.  
Since that night, every time Dean and Sam were anywhere near your tiny Midwestern town he stopped in to do what he called a ‘regular check-in.’ Sometimes he would call first, or text that he was coming over. Other times, he would show up unannounced. When you weren’t there right away, Dean usually found his way over to the bar and would come over afterward a little drunk. You never really minded because he was always respectful and would crash on your couch. There were even times where he would bring Sam with him and they would both take up your living room furniture.  
Dean’s presence was starting to be a regular thing, and you didn’t mind. At first, you were a little awkward, but now he was almost like family. Plus, he was pretty nice to look at, let’s face it. As time went on, you forced yourself to look at him more as a gay best friend or a brother. It was easier than the thought that he wasn’t attracted to you, especially because you were clearly attracted to him.  
Today though, you had been at work when Dean messaged that he was coming through town. Apparently, he dropped Sam off with some guy named Bobby, who was like his dad. This wasn’t the first time you’d heard the name, and you had long ago figured out that Bobby must live nearby because that seemed to be where Sam would go when Dean came over for his 2 or 3 day stay with you. Of course, with you at work, you figured Dean would be coming over a little drunk tonight and boy were you right.  
Now, you had been home for two hours and Dean had just arrived. That dopey grin on his face that was almost too adorable told you everything as you ushered the gorgeous hunter inside.  
“Hey beautiful, how are you?” He slurred a little, which meant this was one of those times where you needed to get him some water and put him to sleep on your couch.  
“I’m doing well Dean, pretty well. Come in and let’s get you out of those shoes and that coat.” You ushered him in, and he slumped onto the couch. You were quick to help him remove his coat and take off his shoes.  
“You know, I can do that myself.”  
“Would you just stop? We can talk more tomorrow, but for right now you need some sleep drunky.”  
“Why don’t we have some more drinks together and then we can both be happy?”  
“Because you need to sleep, and I’m tired too. We can hang out tomorrow alright.” And with those words, you got up pouring him a glass of water from your fridge. When you returned, he already had his eyes closed and his breathing had evened out. You put the drink down on the coffee table out of reach a little so he wouldn’t hit it if he had one of those damn bad dreams that woke you both up sometimes. A quick blanket thrown over him and you were heading to your room.  
That familiar calm surrounded you as you lay there, feeling the protection that came with having a hunter in the other room. You read a few chapters of your book and crashed out. The door to your room was open, and unlike usual you slept in shorts and a tank top. After all, the last thing you needed was for Dean to see you naked. You didn’t need to see the disapproving look in his eyes at the sight of your less than perfect physique.  
You left the door open, of course, because Dean might need something and the motherly part of you always wanted to take care of your savior. After the first time he stayed, you knew he had demons. That first night, Dean woke up yelling in his sleep and you had raced out of your room to see what was going on. He looked at you terrified and you had gone to his side holding him a little, until things calmed. He never wanted to speak about what was in his dream, but he was so thankful to have you there. That much you knew.  
Of course, the bad dreams were better than the other two alternatives. There was the situation that you worried about a little tonight. When Dean had a bad time, he would drink a little too much and after the night he threw up all over your floor trying to find the bathroom, you were always on the lookout for the sound of him stumbling about so you could jump out of bed to help him. And finally, there was that unfortunate night where he was having some sort of PTSD flashback and was wandering around your apartment with his gun drawn. It ended with you terrified, and him visibly shaken. The shock of him storming around had you worried about going to sleep without knowing if he would throw your door open and take a shot.  
All of that added up to you asleep soundly, but with one ear out for your guest to make sure he was okay. That’s why you heard the noises at around 3 am coming from the living room. It was rustling that woke you at first. Your eyes popped open just a little, taking in the sounds to determine if it was worthy of you getting up or just him rolling over. When you heard the sound of Dean breathing heavier in the other room, well that was a signal. You figured he was probably having a bad dream.  
The dim lamp in the corner of the living room was the only light source as you crept down the hallway in your dark apartment listening. You would usually watch him to see if it was bad enough to wake him. There were times, he would wake a little and just roll over. You always tried to preserve his dignity by not being seen when it was just one of those. Something inside told you there was a whole lot that Dean had seen in his life that caused his nightmares, and the last thing you wanted to do was highlight that dark part of him.  
Now, though, you heard a rhythmic shuffling and Dean’s breathing was heavy. Fearing the nightmare was truly horrific, you made your way to the edge of the hallway. You could hide in the shadow here but still see all of Dean. Your face flushed immediately as you took in the full appearance of him before you.  
Dean had his jeans undone and those and his boxers were pushed midway down his thighs. His shirt was drawn up exposing his gorgeous chest and abdomen, a tan landscape of hotness that was only broken up by a few scars. As if being on display like this wasn’t enough to make you turn crimson, there was what Dean was doing. He had one hand stroking over one of his nipples in time with his other hand that stroked up and down his cock. It stood magnificently out, making your body quiver. You had never seen Dean in any real state of undress, but here he was and you could see every inch. Dean’s cock was bigger than you expected and even his large hand didn’t take away from the girth that was there. It was truly a riveting sight.  
You should have left, but it was paralytic to watch him stroke up and down, playing with his tip every so often as a bead of precum would gather. His every sigh and moan had you in suspension as you watched him move faster and faster. If his eyes weren’t opened here and there, you would have sworn he was jerking off in his drunken slumber. But, no, he knew exactly what he was doing – just not what he was doing to you. The crush you had on him forever was never going to go away if you kept watching as he jerked himself off on your couch.  
“Huh…oh [Y/N]...yea just like that beautiful.” Holy fuck, he just whispered your name. You froze, not sure what to make of what you just heard, but knowing that you were going to watch this to its inevitable conclusion.  
“Uh…yes…oh you’re gonna make me cum baby. Uh…huh…..oh [Y/N].” With the last sigh of your name, Dean tilted his cock a little and looked down watching just as you were as cum shot across his stomach. It was mesmerizing to take in the sight of it. Dean’s face pulled tight in pleasure, and then relaxed completely when he finished and lay there breathing heavily as he came down.  
You watched him for another moment, until you saw him shift on the couch, carefully holding up his shirt as he reached over to your tissue box. Then, you panicked in your mind and scampered quickly down the hallway and back to your room. The last thing you wanted was to be caught spying on Dean like that.  
From your bed, you heard him a few minutes later make his way into the bathroom in the hallway. He ran the water a little, and flushed the toilet before you heard tentative footsteps come down the hallway to your room. You heard him enter your room as you lay there curled up with your head buried in your pillow.  
“God you’re beautiful when you sleep. Fuck I wish I could hold you. Sleep well [Y/N].” He whispered the words as you pretended to sleep. How could this be happening? How could Dean even be thinking about you that way? He had told you about dozens of hot women and I mean come on just look at him. This was Dean Winchester and for some reason he was saying those things about you.  
Long after Dean left and you heard him plop down on the couch again, you lay in bed pondering those questions. It was all so much and when sleep finally came back to you, your dreams were filled with oddities that signaled your anxiety.  
************************  
The next morning you awoke to the usual. Dean was in your kitchen, coffee in hand, making breakfast. You had learned to always have some bacon on hand because he loved to make that as well as those damn crescent rolls that you bought tubes of at the store. He always wanted to make a full breakfast while he was with you, insisting that he didn’t get to eat like this when he was on the road doing cases.  
“Good morning, feeling good or hungover today?” You started off simply as you pulled your sweatshirt down over your tank top. You never wore a bra under those, so you weren’t about to give Dean a show he may not want. Although after the night before you were starting to wonder. Mostly, though you were wondering if you had dreamed the whole thing up.  
“I’m doing alright. Thanks for the water. I got up in the middle of the night, had water and aspirin and it seems to have done the trick.”  
“Great! So, you guys just finished a case?”  
“Yep, Sam says hi by the way. We finished a Rugaru case, and then Bobby needed some help so we came through this way.”  
“Always happy to have you, even when you’re a little drunk.”  
“Yea, sorry about that. I had to kill time, and well….you know..”  
“You know I don’t mind. So, how about a movie today once we’re up and ready? There’s a few classics showing at the cheap theater and we can get the matinee price. Maybe some crappy popcorn and candy, and then after pizza?”  
“[Y/N], I swear it’s like you can read my mind.” He smiled that devilish grin at you and a flash of him half naked flooded your mind. What the hell were you supposed to do with what you saw the night before? Nothing you supposed, at least that’s all you had the guts to do about it. There was absolutely no way you were going to make a move on Dean after all. The rejection would kill you.  
The rest of the day found the two of you hanging out like the buddies you had become. When Dean was in town, it was like being a teenager again. He would agree to do anything with you and you were happy to oblige. You always had something in the back of your mind for the next time he came.  
That night proved uneventful, and by the next morning, you knew he was heading out. Breakfast that morning seemed quiet, almost like he was going to miss you. You weren’t sure what was going through his head, but you missed him too. It was just something neither of you said to the other. There was no heavy emotion mixed into any of the conversations you had. It was just fun hanging out and then a little small talk. Sure you would talk about your past or the cool things you were up to, but never anything beyond that. Even when the thoughts of Dean maybe never coming back invaded your brain, you still couldn’t bring it up. There was no reason to sour this incredible thing you had whatever it was.  
***********************  
Dean visited another two times in the next four months, and no more awkward situations happened. It was when he left the second time that you had finally convinced yourself that it was either a dream of yours or a weird fluke that you caught him doing that. Maybe he had met a girl with the same name on some trip, and you had stumbled on him fantasizing about her. Either way, it was a dead issue.  
The next six months were long. Dean hadn’t texted or called and you started to wonder if that was it. He had been a temporary friend in your world, and now you just had to get past him and hope he was okay. You never messaged him unprompted. He had told you that you shouldn’t just in case someone got his phone. He didn’t want you to be exposed to anyone or anything in his world. That way, you wouldn’t be in danger. So, now you were just left to pine after someone that had never really wanted you anyway. That dreamy mystery that was Dean wasn’t coming back.  
It was a quiet Friday night after that realization that found you in your living room curled up on the couch eating ice cream and watching some scary movie when another knock came. It had been a long day at work and you weren’t expecting anyone, although on occasion one of your friends or a neighbor would stop by to chat. The one person you didn’t expect to see was the man standing on the other side of the door.  
“Hey beautiful. How are you?” Dean’s smile took your breath away, and you let your excitement get the better of you. You pulled him inside and wrapped your arms up around his neck. A quick movement and your lips met his without even thinking.  
You pulled back instantly at the touch, fearing the worst and looked at him.  
“I’m so sorry. I didn’t mean to Dean. I was just so worried that you were gone and seeing you….. Well, I’m sorry I was just relieved.” You blushed as you backed up and watched him carefully. He turned pushing the door shut and throwing your deadbolt without a word.  
“Are you sorry like you didn’t ever want to kiss me or are you sorry that you did it then?” His question had you on edge and you wondered how he had formed such a coherent thought when you could hear the slur in his voice that signaled he was a little drunk.  
“Um….the second one.” He approached you and you backed up. Dean lowered his head a little, staring at you like you were prey for a second. You weren’t sure if he was angry or drunk or what, but that was a look you hadn’t seen from him before.  
“I’ve been waiting for almost two years for you to kiss me, so don’t apologize for doing it now.” He stalked towards you and you backed up until you hit the wall at the edge of your kitchen. He continued until he was only a few inches from you and tilted your head up with two fingers beneath your chin. “Baby…do you want me to kiss you?” His words were slow and thick as he spoke, eliciting a carnal response from your body. Moisture filled your panties as you looked from his eyes to his lips. Goosebumps erupted across your skin as time stood still.  
“Yes.” A single word and Dean leaned in claiming your mouth. The heat and softness of his lips surprised you as you let the taste of whiskey and beer slide into your mouth with his tongue. He moaned softly as he kissed you deeper and deeper, pausing only to switch sides with his head.  
You were a mess by the time he moved to your jaw; only able to think about all the times you had dreamed of this moment, hoping desperately that Dean would claim you as his. His tongue slid haphazardly over your throat and you pushed your hands under the shoulders of his jacket. He got the hint, quickly shedding it without even stopping his onslaught on your neck.  
His body pinned you against the wall with his hips flush to you holding you steady. When your fingers threaded into his hair, he groaned. Nails across his scalp had him leaning down to seize your ass in his fingers pulling you from the floor. You wrapped your legs around him and he carried you to the bedroom. No sooner did he throw you on your bed than he was stripping off his clothes like a mad man. You were transfixed, taking in each inch of freshly exposed skin and drooling as you watched. When he was down to only his boxers, he flung himself at you reconnecting with your mouth even as you tried to get your bearings.  
He had you pinned and was soon making his way down your skin. When he reached your neck, he let his hands move downward taking the hem of your t-shirt and pulling it up over your head exposing your flesh. His lips seized on a nipple and his tongue flicked over it lightly. You were moaning before long and when he started to head downward you held your breath. Your imperfections seemed to not matter to him, and you felt like a goddess as Dean peeled your shorts and panties from your body.  
He laid a few kisses along your hips before rejoining your mouth. His fingers brushed along your already wet core and you groaned at his touch. Your hand moved down his stomach taking in the muscles that you had only looked at before.  
“Dean, please….” You needed him now. It was wonderful to have his fingers on you and maybe someday you would get past your insecurities and want his mouth on your pussy as well. Today, though, all you wanted was to feel Dean inside of you. Your pussy ached for him.  
“What baby? Tell me what you want.” He cooed the words out, the whiskey scent ghosting from his lips still as he looked down at you.  
“You….please…I want you inside me.” You whispered it staring into his eyes with intention.  
“Condom?” A single question had you reaching the nightstand by your head and pulling it open. You produced a foil packet and then stopped to take a quick look to assure it wasn’t expired. You didn’t really use them very often to be honest.  
When you turned back, Dean had his boxers off and was eyeing you eagerly.  
“You want to do the honors or shall I?” His smile was wide as he spoke, and you could think of nothing more that you wanted in the world than to put a condom on this god of a man so he could take you.  
You didn’t respond, just tore open the packet with your teeth and reached down. At first, you thought you were being stupid, but then you realized why you were having trouble. Dean wasn’t hard, not even a little. The proud cock you saw cum so many months ago hung limp against his leg. You would say nothing, you decided, and instead assumed he had that much control. Your fingers wrapped around his soft shaft and you moved up and down. He hummed a little, but still nothing.  
“You need help beautiful?” He asked the question and you looked up into his eyes. Your mind reeled and all your anxiety flooded in.  
“Dean, I can’t because…well you’re not hard enough.” There you said it, but the words made your heart sink.  
“What?” He looked a little puzzled and then glanced downward. A shock registered on his face. “Shit, um…give me second.” His own hand came down and he gave his soft shaft a few pumps. “I’m sorry, this…shit…this never happens.”  
“It’s okay. I understand.” In your mind, his body had responded the way he would have sober. He didn’t want you, not really. All that excitement and everything was a show, a response to the pity he felt for you and nothing more. Your heart sank and your self-esteem sank even faster. The great Dean Winchester was trying to force himself to get excited by you.  
“Hang on maybe if I…” He reached out his hand and latched on to your breast kneading it gently. A wave of disgust flew through you and you pushed him away. You stood up from the bed searching for your t-shirt and your shorts.  
You didn’t speak as you started to put your clothes on. Dean lay there for a second as if stunned.  
“Hey wait, don’t do that. Come here and let me take care of you.” He reached out and you couldn’t even make eye contact with him.  
“That’s okay Dean, you don’t have to.”  
“I know. I want to. I don’t know why my body’s not cooperating.”  
“It’s not cooperating because you can’t force yourself to be attracted to me. It’s alright. I know I’m no prize.” The last word came out with a tear that welled up in your eye as you moved to your desk and pulled a sweatshirt from your chair further covering yourself from his eyes.  
“I’m not forcing myself. I….this isn’t you…I mean it must be the booze.” He sounded so beside himself as he spoke, but you still didn’t look up.  
“Forget it….I just…I have to go to the bathroom.” You left quickly and made your way into the bathroom in your hallway. In another minute, you were on the floor with the door locked crying silently into your hands.  
You stayed there for what seemed like an eternity. When you heard no sound for a while, you slowly opened the door peeking out. You could just see into your room, and there was Dean sprawled out snoring lightly. You closed the door behind you and made your way out to the living room. The world had crashed around you and you had no idea what you were going to do next. Dean was practically your best friend and you had ruined it all by coming on to him when he was clearly too drunk to say no. Now, he couldn’t even force himself to be with you, and that gave you the final signal. There was no way that you were recovering from this. After your excitement at seeing him, now you knew that you would never see him again.  
A few hours of pacing, and you finally wrote a note for him. You threw on flip flops and grabbed your purse slipping out of your own apartment at about 5 am. You taped the note to the back of the door and let it close softly.  
It said what you didn’t have the guts to say in person:

“Dean, I’m sorry I tried to force you to be with me when it’s not what you wanted. I wish I hadn’t because now I know what a fool I was for hoping. Can you please leave before I get back? I can’t bear to see you right now. And I’ll completely understand if you never contact me again. Thank you for all the fun times and please remember me without the embarrassment of what I did last night.”  
A few hours later, after a quick breakfast and a mini nap in your car, you pulled back up to your apartment with caution. When you saw that the Impala was gone, you parked and made your way up the stairs to your place. When you went inside, you searched through the rooms, assuring that Dean was gone and then sat down on the couch. Your phone sat on the coffee table, and you breathed a sigh of relief because you thought you had lost it somewhere when it wasn’t in your purse.  
You picked it up to see if there was a message, and found a note folded up on the table beneath it. The paper was folded up into fourths and you didn’t unfold it. After the night before, you just wanted to forget Dean Winchester and you figured you knew what that note was going to say. It would be full of apologies and trying to make you feel like you weren’t the ugly, fat girl that you knew you were. That was the last thing you needed was more pity from Dean Winchester.  
At some point that day, the note went into your room, in the back of the paperback you were reading and that was that. There were no texts or calls from Dean on your phone and your life went back to normal. The occasional memory would surface over the next few months and you would push it out of your mind, hoping that it would fade as time went by. The note made its way from one novel to the next as the months went by.  
*************************  
Everything seemed to be okay until the day you pulled up to your apartment and saw that familiar black Impala parked outside. Your heart sank. The thing you had been avoiding all along could no longer be avoided. Dean had come to put the final nail in your coffin after six months of not seeing or hearing from him.  
You grabbed your bag and made your way up the stairs. Sure enough, the gorgeous man sat on the floor outside your door as you approached. When you stood before his feet, he lifted his head in silence.  
“Why are you here?” The question came from your mouth as you marshaled your best defense against the hurt you felt at seeing him again.  
“You didn’t call or text so I wanted to hear it from you in person.” He said the words as he stood up.  
“What are you talking about?” The words he said didn’t make sense – hear it from you in person? What the hell did that mean?  
“You got my note right? So, you didn’t text me or call me to answer. I gave you six months to the day and nothing.”  
“Dean I got your note, but I didn’t read it.”  
“What? Are you kidding me? I’ve been waiting for six months to get an answer and you didn’t even read it? Well, do you still have it?”  
“Maybe. What does it matter? I know what it says. Just go away Dean.” The words stung you as they came out.  
“No. I’m not leaving until you read the note I left. Now, go inside and get it and come back here so I can watch you read it.” He was stern, almost frightening as he spoke and grabbed your arm pointing at the door.  
You went inside heading for your latest book and pulled the note from the back cover. A quick walk back outside with only your keys and the note and you suddenly understood the fear that Dean could put in someone. You felt like you had to obey him, there simply was no other option.  
“Good, now open it [Y/N].” You looked at him briefly before unfolding the stiffly creased paper. Your eyes went to the first word and you swallowed thickly.  
“[Y/N], I’m not sure what to say to you. I know why you locked yourself in the bathroom and why you left. It’s because I’m a piece of shit asshole. I waited all this time to finally do what I wanted to from the moment we met, and I fucked it all up. Please understand that you didn’t force anything and you have nothing to be sorry for. And, you’re no more of a fool for hoping than I was. The difference between us is that your body worked when you needed it to and mine was so full of whiskey that it apparently couldn’t. You have no idea how many times I have thought about you and been rock hard and yet for whatever reason I couldn’t get hard when I finally had the chance to show you how I really feel. [Y/N] know that I love you, truly love you and I think you are the most beautiful woman I have ever seen. Despite all my stories, I haven’t touched another woman or even thought of another woman since I’ve known you. No other woman compares for me. I hope you read this and can think of me without the idiocy and embarrassment of what I didn’t do last night. Please message me or call me to tell me if you feel the same way or if you just want things to go back the way they were, because I can’t stand not having you in my life one way or the other. I’ll wait until you respond to come back. – Dean”  
You finished the last words and looked up into his eyes. He was pleading with you for an answer with no words. Suddenly, you saw it there, the dread, the hope, the way the six months of no contact had weighed on Dean.  
“Well…don’t leave me hanging here [Y/N].” He searched your face for an answer.  
“I…I thought you were just doing that because you felt bad for me…I…” You didn’t know what to say to his letter, no ideas would come to you.  
“Are you kidding? I figured all the times you let me stay here and hang out you felt bad for me. I have only pitied you once and that’s when you lost your family. I’ve watched a strong, beautiful woman since then, and just prayed that she would see me as more than a friend.”  
“What?”  
“You kissed me that night, and I wanted so badly to believe you felt the same way. When you said yes, I wanted to give you every ounce of feeling I had for you that night. And then when I had whiskey dick….fuck…I was so angry. I waited for you to come out of the bathroom and then I fucked up again passing out. When you left, I just fucking lost it. Then, I waited for you to get in touch, just waited and nothing.”  
“Dean, I didn’t know. I mean look at me and look at you. Why would you ever….” A tear came into your eye and you scanned his face for an answer.  
“Why would I ever what? Drive 6 hours from where I live and pretend I was in the area just to see you for a day? Why would I force my brother to stop with me the one time we were only 2 hours away? Because I fell in love with you, that’s why. And, I never want to hear you say that you aren’t beautiful or question how your body looks. You damn near killed me when I got you naked. I haven’t been able to get that incredible picture out of my head, and trust me I had no trouble getting hard thinking about just how you looked.”  
“Jesus, you really lied to me all those times about being in the area?” The question slipped out as you let everything sink in.  
“Would you stop asking stupid questions and let me in so I can finally show you how I feel?”  
Your words ended at the sound of gravel in his voice. You opened the door and went inside letting him follow. Dean turned locking your door. He stopped there, leaning down and took off his shoes. He pulled his flannel shirt off and tossed it towards the couch. You were frozen not sure what would happen next.  
“Don’t just stand there, strip. Or, I’ll have to undress you.” Your eyes opened wide at his words and you stood staring at him like a deer in headlights. “Okay, you asked for it.”  
Dean rushed at you seizing you by the hips and throwing you over his shoulder like a sack of potatoes.  
“Dean? What the hell are you doing?”  
“What I should have done a long time ago.” He said the words gruffly and you went along for the ride.  
When he reached your bedroom, Dean bent down standing you on your feet. Then, his hands were on you. He peeled your t-shirt up and off of you. His fingers unsnapped your bra quickly and both items found their way to the floor.  
“Hello ladies, I’ve missed you.” He gave you a slight grin and dropped to his knees. Your shorts were undone and being pulled off in the next instant he was pulling each of your shoes off. When he was done there, your panties followed leaving you stunned and naked at the foot of your bed.  
“Um…okay.” It was all you could say as he stood back up and looked you up and down. Your hands went up to cover yourself, and he gently guided them back to your sides.  
“Shhh…just let me look for a second.” He pressed his fingers to his lips as you stood there waiting, terrified. “Alright, now raise that beautiful face for me.” You complied, waiting for his next command.  
“There we go perfection. [Y/N] you are completely perfect. I love your face. It’s so kind and bright, and god those eyes haunt me.” He walked up placing his hands on the side of your face and tilting it up to look at him. His lips descended placing a kiss on your lips softly before he pulled back again.  
“I love your neck, it’s so soft. He leaned down placing a kiss on the side right in the spot that made you shiver.  
“And, these, well my god they are a work of art.” The back of his hands grazed your breasts as he looked into your eyes. His mouth descended then as his arm went behind you leaning you backward so he could place a kiss on each of your nipples.  
In the next moment, he picked you up and laid you back on your bed while he still stood at the foot looking you up and down. You were still taking all this in, trying to make it make sense and afraid to make a move and end it.  
“This stomach, is so beautiful. I love the way your sides dart in leading me down exactly where I want to be.” He knelt down and placed a kiss on your belly button and you sighed.  
“Oh, these hips, my god, how juicy. I have wanted to taste these so bad since I left here.” He kissed each of your hip bones before leaning to the side and licking a stripe up your left outer hip. He moaned at the taste.  
“Dean…I…..”It was your first interruption and met with a quick look.  
“Nope, no talking yet.” He raised a finger at you. “Now, these feet are just perfect. You always have your toes painted, and it drives me crazy. I wonder every time I show up what color will be on these and I’m never right, not once. Even now, I figured yellow for summer, but no they’re silver. I mean silver?” He kissed along the top of one foot and then the other.  
“Now these legs drive me crazy. You wear those damn sleep shorts every time I’m here and I think about how soft they look. You have this silky smooth skin, and I can’t wait for you to wrap those sexy legs around me.” Dean placed alternating kisses up your legs softly caressing the skin in a perfectly chaste way that was making you get hotter by the second.  
A grin spread across his face as he stood up. Then, in a flash he flipped you over on your stomach, scooting you a little further up the bed as he did it.  
“Your back is even beautiful, damn. I mean I don’t think I’ve even seen these little butterfly tattoos, but now….well…” He leaned down placing kisses across your shoulders where you had a dozen small butterflies tattooed dancing across the skin.  
“Now as for this ass…I mean come on. How can a guy look at this ass and not have dirty thoughts. You have got to have the hottest ass I have ever seen on a woman.” He placed a kiss on each of your butt cheeks and then flipped you over with ease once more.  
“Then, there’s my favorite part. The one place I didn’t get to see that night, just feel. Fuck, I didn’t want to wash my hand after I left. I could smell you on my fingers and it was driving me crazy. I almost cried when I had to take a piss because I knew I wouldn’t smell like you anymore. But, now….”

 

Dean motioned to you to slide up the bed and you did as ordered making your way to the pillows. This was all so surreal and you wanted nothing more than to do as he asked.  
He climbed onto the bed at your feet and reached one arm over his head pulling his shirt off easily. Dean’s pupils were blown wide with lust as he leaned down circling your legs with his arms. He planted a slow kiss on each of your inner thighs and then dove into your pussy. It started with slow kisses along every surface and then he plunged his tongue into your wet heat.  
“Oh fuck Dean.” The words sighed out of you on their own as he continued. His tongue slowly circled your clit and then just as quickly as he began he stopped. Your eyes had gone shut and now you opened them looking down at him.  
“There you go, now keep your eyes open. I want you to watch how much I enjoy you.” You focused on his face as he went back to licking and sucking at your core in ways that had never been done to you. With everything, you had forgotten how nervous it made you to be eaten out. Now, you were completely caught up in the feel of Dean’s hot breath on you and how good it felt.  
“That feels so good Dean.” You spoke to him as he looked at you with nothing but lust on his face.  
“Good. Lay back and just come undone for me.” He sounded like pure liquid sex from between your legs and all you could do was comply. In another moment, a finger slid into your dripping core. He drug it out slowly stopping as the tip hit that perfect spot of flesh inside.  
You gasped and your head fell back, eyes closing automatically.  
“Hey, eyes on me.” He tapped your inner thigh startling you. Your eyes opened and your head tilted forward. He smiled and went back to his ministrations on your clit.  
“Fuck, you’re so tight. Gonna feel so good on my cock.” He moaned into you as he slid a second finger inside joining the first.  
“That feels so good….oh, oh…Dean…please.” You panted now feeling your muscles tighten as his lips pulled your clit in.  
“Please what? Tell me what you want [Y/N].” He growled as a third finger slid into you and you moaned out loudly.  
“Please make me cum…I’m so…close.” You could barely think as you stared down into his burning green eyes. He was so insanely hot right now and completely focused on you.  
“I want to make you cum all night.” He said the words before sucking on your clit with full force and pulling all of his fingers up at once. He rocked them against the bundle of nerves inside connecting every place that felt good on you at once it seemed and you cried out his name. A hand flashed out and grabbed the back of his head as your pussy pulsed against him and around him at the same time. The orgasm ripped through you and you were left to pant and moan in its aftershocks as he pulled his fingers from you.  
Soon he was up hovering his face in front of yours.  
“Now, do you understand how beautiful you are?” He stared into your face holding your chin so you faced him as he held himself above you.  
“Dean…I…”  
“Say it. Tell me you’re beautiful.” He held you there transfixed.  
“I…I…”  
“Come on baby say the words. I want to hear you say it and believe it.”  
“I’m beautiful.” It took everything in you and you felt a wave of strange relief and realization wash over you.  
“That’s my girl, now are those condoms expired by now?” He smiled at you and captured your mouth before you could answer.  
You reached over to the nightstand, pulling a packet out and looking at the date. Thank god the answer was no.  
“Nope, still have a few months. You saw me check last time?” You smiled faintly at him.  
“Baby, I remember everything from last time. Now, what do you say you try to put it on me again?” He smirked at he rolled onto his back undoing his jeans. They slid off easily and his underwear soon followed. And your eyes fell to his dick, which stood hard and proud already dripping.  
You opened the foil packet and this time slid the condom on him easily. It felt so good to have that hot skin on your hand, and if you weren’t so damn excited you would have paused to give it a few strokes. You wanted him though, more than anything.  
“[Y/N] that’s all because of you. You made me that hard, not when I was eating you out. Oh no, long before that. The moment I even think about you my body responds. Do you believe me?”  
“I…I want to but…”  
“Whoa, no buts, that’s the truth. I want you and only you. You turned me off from any other woman but you, so don’t you dare question if I want you. This cock only gets hard for you now. So, tell me what you want to do with your cock.” His words were thick with sex and you looked into his eyes searching for some deception. There had to be something wrong with this picture as you looked at the sexiest man you had ever known. But, no, it was just Dean, full sincere, open Dean.  
“Please fuck me, please.”  
“On one condition.” Dean rolled himself over your leg settling into a comfortable place with his lower stomach on your curls.  
“What?” You were breathless with anticipation as he slid himself up until just the tip of his cock was at your entrance.  
“Tell me you’re beautiful again.”  
“Why Dean?”  
“Because I’m gonna make you say it constantly until you believe it. I want you to see yourself the way I see you.” Your eyes welled with tears again as you looked back at him.  
“I…I’m beautiful.”  
“That’s my girl.” He moved up taking your mouth with his and slid himself inside of you slowly. It stretched you so well and reminded you of just how long it had been since you had been with anyone else. It was before your parents died, and the faint stings reminded you of that.  
When Dean was fully seated inside, he pulled his mouth away staring into your face.  
“Are you okay?” His words pulled you from your focus on breathing and adjusting and you looked at him.  
“Yea...just need a minute to get used to my beautiful cock.” You whispered it as you breathed slowly willing your body to relax and enjoy this moment.  
“I’ll try, but you feel so good…I mean…..unh you’re so tight.” He was almost shaking trying to hold himself back and you were the goddess again in your mind. You had Dean Winchester inside of you and he had to use every ounce of strength to keep from pounding into you.  
“My cock, my rules Dean.” You smirked at him and he groaned at you.  
“Keep talking like that and I’ll take it back.” He moved down sucking a mark onto your neck and you groaned as he pulled himself out a little and slid back in slowly. You gasped and he growled at the sensation.  
Dean came back to your mouth as he thrust into you again and again. His speed increased and both of your sounds kept pace. He was even hotter than you could have imagined. Sweat gathered on his skin making it slick as it slid along yours and his face made every sexy expression you could think of with each movement. You were lost in him, the pure sex that was Dean.  
“I’m not gonna last baby, I’ve wanted you too long.” He groaned now as he paused for a second. His breathing was heavy as he hovered above you. One arm propped him up as he slid the other between your bodies. His thumb soon parted your curls and found your clit and you moaned out throwing your head back.  
“Oh Dean…I…”  
“So beautiful when you’re like this.” He sighed and started to move in and out of you again. You could feel the throbbing start in your pussy and your clit was becoming so sensitive. Every stroke of that thumb had you paralyzed. “Wrap those legs around me, come on, please baby.”  
You kissed his lips as your ankles locked behind him. His tongue explored you as he moaned. The movement of his hips grew faster as you held onto him. Your hands moved up and you grabbed his biceps anchoring your whole body to him.  
“Fuck….too good. Unh….oh [Y/N]…yes…just how I imagined this. Dig those nails in beautiful, show me how good it feels.” He was growling the words as he grunted with each thrust. Dean was completely wrecked above you, and you were the same below. The connection you had was like nothing you had ever felt before, and you were beautiful. You were truly beautiful right then in Dean’s eyes and your own as your bodies arched towards bliss.  
“Dean…I….I….” You tried to warn him, but your muscles all contracted and the orgasm slammed into you with full force. You cried out his name and your nails caught into the flesh of his arms.  
“Sweet jesus….” He whispered the words as you felt your pussy pulse around him. His arm flew from your clit to the mattress beside your head catching him as he locked up, thrusting himself deep inside of you.  
His eyes closed and his face contorted as his hips reflexively moved against you, and you stared at him feeling yourself tighten once more. In another second, your core clenched tightly and you came again. He cried out unintelligibly and his eyes flew open. You lay there, paralyzed in pleasure, you felt every nerve fire inside of you in pure pleasure.  
“So, so beautiful.” Dean whispered in your ear before planting sweet kisses along your jaw and down your neck.  
“Thank you.” You said it and he stopped instantly looking up into your face.  
“For what?”  
“For making me feel beautiful.”  
“It’s not hard when you look like you do, now say it again.”  
“I’m beautiful.”  
“There you go.” He kissed your mouth drawing you into him with his arms.

**Author's Note:**

> I typically write erotic/fetish romance. Come find me for more at www.patreon.com/dianapowers. I am also on facebook as diana powers. And, I am extremely reachable and active on instagram as dianapowerslit. If you love my work feel free to make requests for more.
> 
> Thanks for reading and hope you guys like the work. I would love any comments, etc.


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